CN112154183A - Polytetrafluoroethylene composition - Google Patents
Polytetrafluoroethylene composition Download PDFInfo
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- CN112154183A CN112154183A CN201980033946.9A CN201980033946A CN112154183A CN 112154183 A CN112154183 A CN 112154183A CN 201980033946 A CN201980033946 A CN 201980033946A CN 112154183 A CN112154183 A CN 112154183A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/004—Additives being defined by their length
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides a polytetrafluoroethylene composition which contains fibrous filler and has excellent stretch processability. A polytetrafluoroethylene composition comprising polytetrafluoroethylene and a fibrous filler, wherein the fibrous filler has an average fiber length of 100 μm or less and a proportion of a fiber length of more than 160 μm of 15 mass% or less.
Description
Technical Field
The present invention relates to polytetrafluoroethylene compositions.
Background
It is known that polytetrafluoroethylene is used by including a filler to improve mechanical properties.
For example, patent document 1 describes a modified polytetrafluoroethylene composition having a specific surface area of 1.0 to 2.0m blended with a copolymer of tetrafluoroethylene and a copolymerizable monomer at a ratio of 1.0 wt% or less2Per g of carbon fiber.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2003-041083
Disclosure of Invention
Problems to be solved by the invention
The purpose of the present invention is to provide a polytetrafluoroethylene (hereinafter referred to as "PTFE") composition which has excellent stretch processability despite the fibrous filler.
Means for solving the problems
The present invention relates to a PTFE composition comprising PTFE and a fibrous filler, wherein the fibrous filler has an average fiber length of 100 μm or less and a proportion of a fiber length of more than 160 μm of 15 mass% or less.
The proportion of the fibrous filler having a fiber length of less than 80 μm is preferably 75% by mass or more.
The fibrous filler is preferably at least one selected from the group consisting of carbon fibers and glass fibers.
The content of the polytetrafluoroethylene is preferably 60 to 97 mass%.
The content of the fibrous filler is preferably 3 to 40% by mass.
ADVANTAGEOUS EFFECTS OF INVENTION
The PTFE composition of the present invention is excellent in stretch processability even though it contains a fibrous filler.
Detailed Description
The PTFE composition of the present invention will be specifically described below.
Heretofore, a PTFE composition containing a fibrous filler has been known to those skilled in the art that although it is excellent in compression creep resistance and abrasion resistance, it cannot be used for stretch processing, and the stretch processability has not been studied. The present inventors have conducted extensive studies and as a result, have found that when a specific fibrous filler is used, a PTFE composition having excellent stretch processability can be surprisingly obtained even when the fibrous filler is contained.
Specifically, the PTFE composition of the present invention comprises PTFE and a fibrous filler, wherein the fibrous filler has an average fiber length of 100 μm or less and a proportion of a fiber length of more than 160 μm of 15 mass% or less. By having the above-mentioned constitution, a PTFE composition excellent in mechanical strength such as compressive strength and excellent in stretch processability can be formed.
The PTFE may be a homopolyptfe containing only a TFE unit, or a modified PTFE containing a TFE unit and a modified monomer unit based on a modified monomer copolymerizable with TFE.
The PTFE may be high-molecular-weight PTFE having non-melt-processability and fibrillating properties, or low-molecular-weight PTFE having melt-processability but not fibrillating properties, and is preferably high-molecular-weight PTFE having non-melt-processability and fibrillating properties.
The above-mentioned modifying monomer is not particularly limited as long as it is copolymerizable with TFE, and examples thereof include perfluoroolefins such as hexafluoropropylene [ HFP ]; chlorofluoroalkenes such as chlorotrifluoroethylene [ CTFE ]; hydrogen-containing fluoroolefins such as trifluoroethylene and vinylidene fluoride [ VDF ]; a perfluorovinyl ether; a perfluoroalkylethylene; ethylene; fluorine-containing vinyl ethers having a nitrile group, and the like. The number of the modifying monomers used may be 1, or 2 or more.
The perfluorovinyl ether is not particularly limited, and examples thereof include the following general formula (1)
CF2＝CF-ORf1 (1)
(wherein Rf1A perfluoroorganic group) and the like. In the present specification, the "perfluoro organic group" refers to an organic group in which all hydrogen atoms bonded to carbon atoms are replaced with fluorine atoms. The aforementioned perfluoroorganic group may have an ether oxygen.
Examples of the perfluorovinyl ether include Rf in the general formula (1)1Perfluoro (alkyl vinyl ether) [ PAVE ] representing C1-10 perfluoroalkyl group]. The perfluoroalkyl group preferably has 1 to 5 carbon atoms.
Examples of the perfluoroalkyl group in PAVE include perfluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, etc., and perfluoropropyl vinyl ether [ PPVE ] in which the perfluoroalkyl group is perfluoropropyl group is preferable.
The perfluorovinyl ether may further include Rf in the general formula (1)1A C4-C9 perfluoro (alkoxyalkyl) group, Rf1Is represented by the following formula:
[ solution 1]
(wherein m represents 0 or an integer of 1 to 4), and Rf1Is represented by the following formula:
[ solution 2]
(wherein n represents an integer of 1 to 4) or the like.
The perfluoroalkyl ethylene is not particularly limited, and examples thereof include perfluorobutyl ethylene [ PFBE ], perfluorohexyl ethylene, (perfluorooctyl) ethylene, and the like.
As the fluorine-containing vinyl ether having a nitrile group, CF is more preferable2＝CFORf2CN (in the formula, Rf)2An alkylene group having 2 to 7 carbon atoms in which an oxygen atom may be inserted between 2 carbon atoms).
The modified monomer in the modified PTFE is preferably at least one selected from the group consisting of HFP, CTFE, VDF, PPVE, PFBE, and ethylene. More preferably at least one monomer selected from the group consisting of PPVE, HFP and CTFE.
In the modified PTFE, the modified monomer unit is preferably in the range of 0.001 to 2 mol%, and more preferably in the range of 0.001 to 1 mol%.
In the present specification, the content of the modified monomer unit constituting the modified PTFE can be calculated by appropriately combining NMR, FT-IR, elemental analysis, and fluorescent X-ray analysis depending on the type of the monomer.
The Melt Viscosity (MV) of the PTFE is preferably 1.0X 10 pas or more, more preferably 1.0X 10Pa · s2Pa · s or more, preferably 1.0X 103Pa · s or more.
The melt viscosity can be measured as follows: according to ASTM D1238, a flow tester (manufactured by Shimadzu corporation) and
the die (2 g) of the above-mentioned die was held at the above-mentioned temperature under a load of 0.7MPa, and the measurement was carried out while heating the sample at the measurement temperature (380 ℃ C.) for 5 minutes in advance.
The Standard Specific Gravity (SSG) of the PTFE is preferably 2.130 to 2.230, more preferably 2.140 or more, and still more preferably 2.190 or less.
In the present specification, the Standard Specific Gravity (SSG) can be measured by the displacement in water method according to ASTM D4895-89.
The melting point of the PTFE is preferably 324 to 360 ℃. In the present specification, the melting point of the fluororesin is a value determined as a temperature corresponding to the maximum value in the heat of fusion curve when the temperature is raised at a rate of 10 ℃/minute using a Differential Scanning Calorimetry (DSC) apparatus.
The PTFE preferably has fibrillating properties. The fibrillation property refers to a property of easily fibrillating to form fibrils. By paste extrusion molding from PTFE having fibrillation properties, a continuous paste extruded strand was obtained, and stretching was observed in the strand (unbaked strand). On the other hand, even if PTFE having no fibrillating property is paste-extruded, a continuous paste-extruded strip cannot be obtained, or even if such a paste-extruded strip is obtained, there is almost no stretching of the unfired strip.
The PTFE preferably has non-melt-processability in addition to fibrillation. Non-melt processibility means that the polymer cannot be melt processed.
The PTFE is preferably PTFE molding powder. The PTFE molding powder is obtained by suspension polymerization of TFE. The PTFE molding powder may be obtained by granulating particles obtained by polymerization by a known method.
The PTFE is preferably in the form of particles, and the average particle diameter is preferably 1 to 2000. mu.m. The average particle diameter is more preferably 1000 μm or less, and still more preferably 700 μm or less. And is preferably 10 μm or more, more preferably 15 μm or more. If the average particle diameter is too large, molding or mixing with a fibrous filler may be difficult, and if the average particle diameter is too small, the flowability of the PTFE composition may be deteriorated.
The average particle diameter of the above-mentioned PTFE particles was measured in accordance with JIS K6891 or measured at a dispersion pressure of 3.0bar using a laser diffraction type particle size distribution measuring apparatus without using a cascade, and was set to be equal to a particle diameter corresponding to 50% of the integral of the particle size distribution. As the laser diffraction particle size distribution measuring apparatus, for example, HELOS & RODOS manufactured by japan electronics corporation can be used.
The PTFE compositions of the present invention comprise a specific fibrous filler. The polytetrafluoroethylene and the specific fibrous filler are contained, whereby the mechanical strength such as compressive strength can be improved and the stretch processability is also excellent.
The fibrous filler has an average fiber length of 100 μm or less. From the viewpoint of further improving the drawing processability, the average fiber length is preferably 95 μm or less, more preferably 80 μm or less, and further preferably 60 μm or less.
The lower limit of the average fiber length is not limited, and is, for example, 40 μm.
As for the average fiber length, 10 visual fields were arbitrarily imaged with 200-fold images by a scanning electron microscope, and the fiber length of 200 fibers was measured to determine the average fiber length (weight basis). Further, regarding the ratio of the fiber length of more than 160 μm and the ratio of the fiber length of less than 80 μm, 10 fields of view were arbitrarily imaged with a 200-fold image by a scanning electron microscope, the fiber lengths of 200 fibers were measured, and the respective ratios were read from the distributions thereof to calculate the fiber lengths.
The fibrous filler preferably has an average fiber diameter of 1 to 25 μm, more preferably 1 to 20 μm, and still more preferably 5 to 20 μm, from the viewpoint of maintaining mechanical strength and mixing property with polytetrafluoroethylene.
As for the average fiber diameter, 10 visual fields were arbitrarily photographed from 200-fold images by a scanning electron microscope, and the fiber length of 200 fibers was measured to determine the number average fiber diameter.
In the fibrous filler, the proportion of the fiber length of more than 160 μm is 15% by mass or less. From the viewpoint of further improving the drawing processability, the proportion of the fiber length of more than 160 μm is preferably 10% by mass or less, more preferably 5% by mass or less, and further preferably 4% by mass or less.
In the fibrous filler, the proportion of the fiber length of less than 80 μm is preferably 75% by mass or more in view of excellent mechanical strength and excellent drawing processability. The above proportion is more preferably 80% by mass or more.
The fiber length was calculated by arbitrarily capturing 200-fold images of the scanning electron microscope for 10 fields of view at a ratio of more than 160 μm and a ratio of less than 80 μm, measuring the fiber length of 200 fibers, and reading the respective ratios from the distribution.
The aspect ratio of the fibrous filler is preferably 2.0 to 8.0, more preferably 2.5 to 7.0, and even more preferably 3.0 to 6.0, in order to improve mechanical strength such as compressive strength and to further improve stretch processability.
The aspect ratio was calculated from the average of the fiber lengths and the average of the fiber diameters of 200 fibers by arbitrarily capturing 10 fields of view of 200-fold images of a scanning electron microscope.
The fibrous filler is not particularly limited, and examples thereof include glass fibers, carbon fibers, graphite fibers, ceramic fibers, asbestos, mineral wool, potassium titanate whiskers, silicon carbide whiskers, sapphire whiskers, aluminum borate whiskers, wollastonite, copper wires, steel wires, stainless steel wires, and silicon carbide fibers; organic fibers such as aromatic polyamide fibers, rayon, phenol resins, and polybenzimidazole fibers; and so on. Among these, from the viewpoint of dispersibility with the resin, at least one selected from the group consisting of carbon fibers, glass fibers, ceramic fibers and organic fibers is preferable, and at least one selected from the group consisting of carbon fibers and glass fibers is more preferable.
The carbon fiber may be any of PAN-based carbon fiber, pitch-based carbon fiber, cellulose-based carbon fiber, and the like. The carbon fibers may be isotropic carbon fibers or anisotropic carbon fibers.
In the fibrous filler, the specific gravity is preferably 1.3 or more and less than 2.0, and more preferably 1.4 to 1.9, from the viewpoint of abrasion resistance. The specific gravity can be determined by the butanol substitution method (JIS R7222).
In the PTFE composition of the present invention, the content of PTFE is preferably 60 to 97% by mass. The content of PTFE is more preferably 70% by mass or more, further preferably 80% by mass or more, and more preferably 95% by mass or less, further preferably 92% by mass or less.
In the PTFE composition of the present invention, the fibrous filler is preferably contained in an amount of 3 to 40 mass%. If the content is less than 3% by mass, the effect of filling the filler may not be exhibited, and if it exceeds 40% by mass, the mechanical properties may be significantly reduced.
The content of the fibrous filler is more preferably 5% by mass or more, further preferably 8% by mass or more, and more preferably 30% by mass or less, further preferably 20% by mass or less.
The PTFE composition of the present invention may contain only PTFE and a fibrous filler, or may contain other components as needed.
As the other components, various additives such as metals, inorganic or organic reinforcing fillers or compatibilizers, lubricants (carbon fluoride, carbon graphite, molybdenum disulfide), and stabilizers may be compounded in combination.
The PTFE composition of the present invention can be produced by a known method. Example (b)For example, PTFE, a fibrous filler and, if necessary, other components are mixed by a V-type mixer, a tumbler mixer, a Henschel mixer, a ball mixer, a kneader, a roll mixer, a kneader,
A mixer such as a mixer, and mixing the components.
The PTFE composition of the present invention is excellent in stretch processability, and therefore can be used by being molded into a sheet, a tube, a ring, a stretched film, or the like. The present invention also provides a molded article obtained by stretching the PTFE composition. The shape of the molded article is not particularly limited, and examples thereof include a sheet shape, a tubular shape, and a ring shape.
The molded article can be produced by a conventionally known drawing method.
The PTFE composition of the present invention can also be used as a sliding material. Examples of products including sliding materials include various gears, bearings (ベアリング) of sliding friction or rolling friction mechanisms, bearings (spindle bearings け), brake devices, clutch members, piston rings, and various seals. Suitable applications include seal rings used in various hydraulic devices such as an automatic transmission and a continuously variable transmission of an automobile. That is, the present invention also provides a seal ring obtained by molding the resin composition.
For example, a desired molded article (such as a gasket) can be obtained by mixing PTFE and a fibrous filler with the above mixer to obtain a resin composition, molding the resin composition by a molding method such as compression molding, firing the molded article at 350 to 380 ℃ for 0.5 to 10 hours, and then processing the obtained fired article by cutting or the like.
Further, the present invention can be used as a seal (end seal, piston ring) for a compressor using carbon dioxide, natural gas, a freon substitute, air, helium, or the like, a high hydraulic pressure seal for a high-rise building, a power steering seal ring for a truck, a bus, an automobile, or the like, and a seal bearing for a construction machine such as a forklift, a bulldozer, a nailing machine, or the like.
Examples
The PTFE composition of the present invention will be described with reference to examples, but the PTFE composition of the present invention is not limited to these examples.
The starting compounds used in the examples are illustrated.
(1) Polytetrafluoroethylene (PTFE)
PTFE(A)
Commercial products: POLYFLON M-18F, available from Dajin industries, Ltd, Standard Specific Gravity (SSG): 2.164, melting point: 344.9 deg.C
(2) Fibrous filler
[ carbon fiber (A) ]
An average fiber length of 53.0 μm, a proportion of the fiber length of more than 160 μm of 0.5 mass%, a proportion of the fiber length of less than 80 μm of 94.0 mass%, an aspect ratio: 3.9
[ carbon fiber (B) ]
An average fiber length of 56.0 μm, a fiber length ratio of more than 160 μm of 3.0% by mass, a fiber length ratio of less than 80 μm of 81.0% by mass, an aspect ratio: 3.9
[ carbon fiber (C) ]
Average fiber length 114.0 μm, proportion of fiber length of more than 160 μm of 21.0 mass%, proportion of fiber length of less than 80 μm of 43.0 mass%, aspect ratio: 9.5
[ carbon fiber (D) ]
An average fiber length of 118.0 μm, a fiber length ratio of 10.0 mass% to more than 160 μm, a fiber length ratio of 52.0 mass% to less than 80 μm, an aspect ratio: 8.7
Various measurement methods of characteristics evaluated in the experimental examples will be described.
Compressive strength
Each of the resin compositions 210g of examples 1 to 2 and comparative examples 1 to 2 was press-molded at a molding pressure of 49.0MPa, and then fired at 370 ℃ to obtain a cylindrical molded article (outer diameter 50mm, height 50 mm). A test piece (outer diameter 10mm, height 20mm) for compressive strength test was prepared from the molded article, and the test piece was compressed at a rate of 10mm/min using Autograph AG-I manufactured by Shimadzu corporation until the height of the test piece was deformed by 25%, and the stress at that time was measured.
Pinhole
Each of the resin compositions 210g of examples 1 to 2 and comparative examples 1 to 2 was press-molded at a molding pressure of 30MPa, and then fired at 370 ℃ to obtain a cylindrical molded body (outer diameter 50mm, height 50 mm). The molded article was subjected to shaving to produce a sheet having a thickness of approximately 0.13 mm. The sheet was stretched at a rate of 50mm/min using an Autograph AGS-J tensile tester manufactured by Shimadzu corporation until the stretching ratio reached 2 times, and the number of pinholes formed in the molded article at this time was observed. In the observation of the pinhole, 10 visual fields were arbitrarily photographed from 40-fold images of an actual microscope, and the average thereof was calculated.
The average fiber length (based on weight), the ratio of the fiber length to be larger than 160 μm, and the ratio of the fiber length to be smaller than 80 μm of the carbon fibers were calculated from the fiber length distribution by arbitrarily capturing 10 fields of view of 200-fold images of a scanning electron microscope, measuring the fiber lengths of 200 fibers, and measuring the fiber lengths.
Example 1
90 parts by mass of a polytetrafluoroethylene resin powder (the above-mentioned PTFE (A)) obtained by suspension polymerization and 10 parts by mass of carbon fibers (A) were mixed by a Henschel mixer to obtain a PTFE composition.
Example 2 and comparative examples 1 to 2
A PTFE composition was obtained in the same manner as in example 1, except that the type of fibrous filler was changed as shown in table 1.
[ Table 1]
As is clear from Table 1, by setting the carbon fiber content of the average fiber length of 100 μm or less and more than 160 μm to 15 mass% or less, a molded article having excellent compressive strength, a small number of pin holes and being less likely to break can be obtained.
Claims (5)
1. A polytetrafluoroethylene composition characterized in that,
comprising polytetrafluoroethylene and a fibrous filler,
the fibrous filler has an average fiber length of 100 [ mu ] m or less and a proportion of a fiber length of more than 160 [ mu ] m of 15 mass% or less.
2. The polytetrafluoroethylene composition according to claim 1 wherein the proportion of the fibrous filler having a fiber length of less than 80 μm is 75% by mass or more.
3. The polytetrafluoroethylene composition according to claim 1 or 2, wherein said fibrous filler is at least one selected from the group consisting of carbon fibers and glass fibers.
4. The polytetrafluoroethylene composition according to claim 1, 2 or 3, wherein the polytetrafluoroethylene content is 60 to 97 mass%.
5. The polytetrafluoroethylene composition according to claim 1, 2, 3 or 4, wherein the fibrous filler is contained in an amount of 3 to 40 mass%.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018097927A JP6750645B2 (en) | 2018-05-22 | 2018-05-22 | Polytetrafluoroethylene composition |
| JP2018-097927 | 2018-05-22 | ||
| PCT/JP2019/019295 WO2019225434A1 (en) | 2018-05-22 | 2019-05-15 | Polytetrafluoroethylene composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112154183A true CN112154183A (en) | 2020-12-29 |
| CN112154183B CN112154183B (en) | 2022-08-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980033946.9A Active CN112154183B (en) | 2018-05-22 | 2019-05-15 | Polytetrafluoroethylene composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20210206946A1 (en) |
| EP (1) | EP3786228A4 (en) |
| JP (1) | JP6750645B2 (en) |
| CN (1) | CN112154183B (en) |
| WO (1) | WO2019225434A1 (en) |
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| JPH0711088A (en) * | 1993-06-25 | 1995-01-13 | Asahi Glass Co Ltd | Polytetrafluoroethylene composition |
| JPH07290582A (en) * | 1994-04-26 | 1995-11-07 | Osaka Gas Co Ltd | Manufacture of graphite fiber reinforced fluoroplastic composite body |
| JPH10254199A (en) * | 1997-03-14 | 1998-09-25 | Ntn Corp | Sliding guide to transfer sheet in image forming device |
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| WO2016114244A1 (en) * | 2015-01-17 | 2016-07-21 | イーグル工業株式会社 | Water-lubricated bearing material |
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| JP2003041083A (en) | 2001-07-25 | 2003-02-13 | Du Pont Mitsui Fluorochem Co Ltd | Modified polytetrafluoroethylene composition |
| JP2003183625A (en) * | 2001-12-20 | 2003-07-03 | Kayaba Ind Co Ltd | Sealing member consisting of polytetrafluoroethylene composition |
| JP3733074B2 (en) * | 2002-01-29 | 2006-01-11 | 三菱電線工業株式会社 | Rotating shaft seal |
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2018
- 2018-05-22 JP JP2018097927A patent/JP6750645B2/en active Active
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2019
- 2019-05-15 CN CN201980033946.9A patent/CN112154183B/en active Active
- 2019-05-15 EP EP19807047.6A patent/EP3786228A4/en active Pending
- 2019-05-15 US US17/057,228 patent/US20210206946A1/en active Pending
- 2019-05-15 WO PCT/JP2019/019295 patent/WO2019225434A1/en unknown
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| JPH02251599A (en) * | 1989-03-27 | 1990-10-09 | Nippon Valqua Ind Ltd | Glass fiber-containing polytetrafluoroethylene composition and molded product thereof |
| JPH0711088A (en) * | 1993-06-25 | 1995-01-13 | Asahi Glass Co Ltd | Polytetrafluoroethylene composition |
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| JP2008208159A (en) * | 2007-02-23 | 2008-09-11 | Teijin Ltd | Heat-resistant heat-conductive composite sheet and heat-resistant heat-conductive sheet |
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| WO2016114244A1 (en) * | 2015-01-17 | 2016-07-21 | イーグル工業株式会社 | Water-lubricated bearing material |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2019225434A1 (en) | 2019-11-28 |
| CN112154183B (en) | 2022-08-16 |
| JP2019203055A (en) | 2019-11-28 |
| EP3786228A1 (en) | 2021-03-03 |
| EP3786228A4 (en) | 2022-01-26 |
| US20210206946A1 (en) | 2021-07-08 |
| JP6750645B2 (en) | 2020-09-02 |
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